(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl](2R)-(2,3,3,4,4,5,5,6,6-2H9)piperidin-2-ylmethanol hydrochloride

• ChemBase ID: 172613
• Molecular Formular: C17H17ClF6N2O
• Molecular Mass: 414.7730992
• Monoisotopic Mass: 414.09336017
• SMILES: c1ccc2c(c1C(F)(F)F)nc(cc2[C@@H](C1NCCCC1)O)C(F)(F)F.Cl
• Canonical SMILES: O[C@@H](c1cc(nc2c1cccc2C(F)(F)F)C(F)(F)F)C1CCCCN1.Cl
• InChI: InChI=1S/C17H16F6N2O.ClH/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11;/h3-5,8,12,15,24,26H,1-2,6-7H2;1H/t12-,15-;/m0./s1
• InChIKey: WESWYMRNZNDGBX-NXCSSKFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl](2R)-(2,3,3,4,4,5,5,6,6-^2H₉)piperidin-2-ylmethanol hydrochloride
• IUPAC Traditional name: (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl](2R)-(2,3,3,4,4,5,5,6,6-^2H₉)piperidin-2-ylmethanol hydrochloride
• Synonyms: (αS)-rel-α-(2R)-2-(Piperidinyl-d9)-2,8-bis(trifluoromethyl)-4-quinolinemethanol; (+/-)-Mefloquine-d9 Hydrochloride; Loriam-d9; Mefloquin-d9 Hydrochloride; Mefloquine-d9 Hydrochloride; NSC 157387-d9; Ro 21-5998/001-d9; WR 142490-d9; Mefloquine-d9 Hydrochloride

Database IDs

• CAS Number: 1217653-15-0
• PubChem SID: 164228523
• PubChem CID: 46782113

CALCULATED PROPERTIES

• Acid pKa: 13.785841
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.94418555
• LogD (pH = 7.4): 2.0721047
• Log P: 4.1105947
• Molar Refractivity: 82.5774 cm^3
• Polarizability: 31.668854 Å^3
• Polar Surface Area: 45.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 242-244°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M207052

Labelled quinoline methanol antimalarial agent.

REFERENCES

• Carroll, F.I., et al.: J. Med. Chem., 17, 210 (1974)
• Davidson, M.W., et al.: J. Med. Chem., 20, 1117 (1974)
• Brown, R.E., et al.: Life Sci., et al.: 25, 1857 (1974)
• Lim, P., et al.: Anal. Profiles Drug Subs., 14, 157 (1974)